PE20020272A1 - N-OXIDES OF 4-PHENYL-PYRIDINE DERIVATIVES AS PRO-DRUGS OF NEUROQUININ-1 RECEPTOR ANTAGONISTS - Google Patents

N-OXIDES OF 4-PHENYL-PYRIDINE DERIVATIVES AS PRO-DRUGS OF NEUROQUININ-1 RECEPTOR ANTAGONISTS

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Publication number
PE20020272A1
PE20020272A1 PE2001000704A PE2001000704A PE20020272A1 PE 20020272 A1 PE20020272 A1 PE 20020272A1 PE 2001000704 A PE2001000704 A PE 2001000704A PE 2001000704 A PE2001000704 A PE 2001000704A PE 20020272 A1 PE20020272 A1 PE 20020272A1
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Peru
Prior art keywords
alkyl
phenyl
trifluoromethyl
oxides
pyridine derivatives
Prior art date
Application number
PE2001000704A
Other languages
Spanish (es)
Inventor
Torsten Hoffmann
Andrew Sleight
Patrick Schnider
Sonia Maria Poli
Original Assignee
Hoffmann La Roche
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Publication date
Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of PE20020272A1 publication Critical patent/PE20020272A1/en

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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

SE REFIERE A N-OXIDOS DE DERIVADOS DE 4-FENIL-PIRIDINA DE FORMULA I DONDE R ES H, ALQUILO, ALCOXILO, HALOGENO, TRIFLUOROMETILO; R1 ES H, HALO; R Y R1 PUEDEN ESTAR JUNTOS CON LOS ATOMOS DE CARBONO DEL ANILLO A LOS QUE ESTAN UNIDOS -CH=CH-CH=CH-; R2 Y R2' SON H, HALOGENO, TRIFLUOROMETILO, ALCOXILO, CIANO; R3 Y R3' SON H, ALQUILO, CICLOALQUILO; R4 Y R4' SON -(CH2)mOR6, ALQUILO; R4 Y R4' FORMAN JUNTO CON EL ATOMO DE N AL QUE ESTAN UNIDOS UNA AMINA TERCIARIA CICLICA DEL GRUPO a ; R5 ES H, OH, ALQUILO, ENTRE OTROS; R6 ES H, ALQUILO, FENILO; X ES -C(O)N(R6)-, ENTRE OTROS; n ES 0-4; m ES 1-3. SON COMPUESTOS PREFERIDOS ESTER TERC-BUTILICO DEL ACIDO 4-{5-[(3,5-BIS-TRIFLUOROMETIL-BENCIL)-METIL-CARBAMOIL-4-o-TOLIL-PIRIDIN-2-IL}-4-OXI-PIPERAZIN-1-CARBOXILICO, ESTER ETILICO DEL ACIDO 5'-[(3,5-BIS-TRIFLUOROMETIL-BENCIL)-METIL-CARBAMOIL-4-o-TOLIL-1-OXI-3,4,5,6-TETRAHIDRO-2H-[1,2']PIRIDINIL-4-CARBOXILICO, ENTRE OTROS. SE REFIERE TAMBIEN A UN PROCESO PARA LA PREPARACION. LOS N-OXIDOS DE DERIVADOS DE 4-FENIL-PIRIDINA COMO PRODROGAS DE LOS ANTAGONISTAS DEL RECEPTOR DE NEUROQUININA 1 (NK-1) SON UTILES PARA EL TRATAMIENTO DE CONDICIONES INFLAMATORIAS, MIGRANA, ARTRITIS REUMATOIDEA, ASMAREFERS TO N-OXIDES OF 4-PHENYL-PYRIDINE DERIVATIVES OF FORMULA I WHERE R IS H, ALKYL, ALCOXYL, HALOGEN, TRIFLUOROMETHYL; R1 IS H, HALO; R AND R1 MAY BE TOGETHER WITH THE CARBON ATOMS OF THE RING TO WHICH THEY ARE BOUND -CH = CH-CH = CH-; R2 AND R2 'ARE H, HALOGEN, TRIFLUOROMETHYL, ALCOXYL, CYANE; R3 AND R3 'ARE H, ALKYL, CYCLOALKYL; R4 AND R4 'ARE - (CH2) mOR6, ALKYL; R4 AND R4 'FORM, TOGETHER WITH THE N ATOM TO WHICH THEY ARE UNITED, A CYCLIC TERTIARY AMINE OF GROUP a; R5 IS H, OH, ALKYL, AMONG OTHERS; R6 IS H, ALKYL, PHENYL; X IS -C (O) N (R6) -, AMONG OTHERS; n IS 0-4; m IS 1-3. PREFERRED COMPOUNDS THIRD-BUTYL ESTER OF ACID 4- {5 - [(3,5-BIS-TRIFLUORomethyl-BENZYL) -MEthyl-CARBAMOYL-4-o-TOLYL-PYRIDIN-2-IL} -4-OXY-PIPERAZIN- 1-CARBOXYL, ETHYL ACID ESTER 5 '- [(3,5-BIS-TRIFLUORomethyl-BENZYL) -METIL-CARBAMOIL-4-o-TOLIL-1-OXI-3,4,5,6-TETRAHIDRO-2H- [1,2 '] PYRIDINYL-4-CARBOXYL, AMONG OTHERS. IT ALSO REFERS TO A PROCESS FOR PREPARATION. N-OXIDES FROM 4-PHENYL-PYRIDINE DERIVATIVES AS PRODROGES OF NEUROQUININ-1 RECEPTOR ANTAGONISTS (NK-1) ARE USEFUL FOR THE TREATMENT OF INFLAMMATORY CONDITIONS, MIGRAN, RHEUMATOID ARTHRITIS, ASTHMA

PE2001000704A 2000-07-14 2001-07-13 N-OXIDES OF 4-PHENYL-PYRIDINE DERIVATIVES AS PRO-DRUGS OF NEUROQUININ-1 RECEPTOR ANTAGONISTS PE20020272A1 (en)

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EP00115287 2000-07-14

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